i vividly remember the first time i ever made a tickling wager…
mike and i were in high school at the time and had both played hooky on a tuesday. we were at my house alone, since both my parents were at work. we started playing basketball early in the day. 20 point games. we became more and more competitive each game we played. we would rub it in and tease the other each time we won. i’d won the first game, lost the two next games, and then won the next two, and then mike won again. after he got through taunting me and we were about to start a new game, he suddenly turned to me “hey, you wanna’ play for something this time?”.
i asked him what he meant. “you know”, he answered, “make a wager on this game, you scared?”. i told him that no, i wasn’t scared, i just didn’t have any money to put up. that’s when his eyes took on a wicked cast, “well… we could play for something else…?” i asked what he meant and he said that we could play that the winner could make the loser do whatever he wanted for an hour. “like what?”, i warily asked. “that’s the fun part, the winner gets to devise any penalty he wants, the anxiety of not knowing exactly what’ll happen to you if you lose will be half the fun!!” i agreed, but was a little nervous about the whole thing, but kinda’ excited about the thought of winning and thinking up something really hellish for him to do. the game began. the wager hanging over our heads made us even more determined to win. we played with an energy and aggression that far surpassed the previous games. by the time it was over we were both soaked with sweat, but i was a happy boy. i won!!! after the relief of not being subject to mike’s whims i began to think of what i might like to do to him. i thought about making him do pushups, or jog for an hour beside my car while i set his pace, i thought about making him kiss my sweaty feet…then it occurred to me!! there had been many occasions in the past when mike’s bare feet had been in reach and i’d stroked em a couple times just to make him jump, so i knew he was ticklish! i wondered what it’d be like to tickle him for an hour while he was helpless. a perfectly evil plan!!! at first mike tried acting as if he’d forgotten all about the bet, but i reminded him and he couldn’t deny it. it had only been half an hour since we’d made the deal. “all right, what do i have to do? wash your car? do your homework? clean your room?” he was obviously thinking along different lines than i was! i looked around. there was a long metal-framed lounger in our backyard. i guided him reluctantly over to it and pulled off all the cushions to reveal it’s metal frame. ” lie down on this.” i instructed. ”’why?”, he wanted to know. ” remember”, i reminded him, “half the fun is not knowing what’s going to happen to you…”. he groaned at me throwing his own words back in his face and plopped himself down onto the patio recliner. i got some pieces of nylon rope from the shed and had him raise his arms above his head so i could tie his wrists securely to the top of the frame. “what? you’re just gonna tie me up in the backyard and leave me like this for an ho ur…ooooh, big deal…” i ignored him and moved down to his legs. i grabbed his ankles and pulled him down the chair till his body was stretched tight, anchored at the wrists. then, with his feet hanging just over the edge of the chair, i tied his ankles down, separately to each corner. i made sure that all his bindings were secure, then i went back to the foot of the chair and sat down in the grass. i remember, looking up into the sky and thinking what a beautiful day this was, and how this was going to be a much better way to enjoy the early afternoon than math class would have been. i pulled on his shoelaces, untying each one, and then slipped his sneakers off to reveal the sweat-drenched white cotton socks plastered to the form of his wide, athletic feet. “hey!!! what the heck are you doing? gonna give me a foot massage?”, he asked, still not getting a clue as to what my plans were. i grabbed the tops of his sweatsocks and slowly peeled the filthy material away from his bound feet. i sat back and gazed at his helpless feet for a minute… “well”, he said ” what now?”. without a word i picked up his smelly sneakers and took out the shoelaces. i used the laces to tie around his big toes, then pulled them tightly back and tied them off around his ankles so that his feet were held in a hyper-flexed position, the skin of the soles stretched tight with no way to budge his feet at all (he could barely even wiggle his toes). “you’re ticklish aren’t you mike?” i asked innocently, even though i already knew the answer. his eyes widened in sudden fear as the realization of what i had in store dawned on him all at once. he panicked and gave himself away “NO. not that!!! that’s the one thing that’s not allowed! NO WAY!!! NO TICKLING!!!” i shook my head slowly, smiling, and told him that i didn’t remember that distinction being mentioned. all i remembered was “anything the winner wants”. well, this was what i wanted. he looked so scared, ‘peeeeease…don’t do this! anything, i’ll do ANYTHING else!!” i cut short his begging when i made contact with all fingertips at once scrambling erratically around the surface of both his soles at once. his begging suddenly caught in his throat and the sounds he was making ceased to be words and became loud, frantic, laughter. his whole body tensed. i could see every muscle of his body (he wasn’t wearing a shirt, just little cotton running shorts) flexed in his agony, but i didn’t let up. i tickled him with my fingers for about ten minutes, enjoying every twitch, every agonized laugh, every fruitless attempt to appeal to my mercy and then began to wonder what reaction other devices might illicit. i excused myself for a couple minutes and went inside. when i returned i had in my possession a stainless steel fork, ice cubes, a feather, a hairbrush, toothpicks, a battery powered toothbrush, and a couple ball-point pens…i showed him the toys i’d collected inside and felt my cock get a little harder as i watched his reaction. he looked as if he were about to cry as his gaze darted, in horror, from one hous ehold-item-turned-instrument-of-torture to another! “no…please…no…”. i made myself comfortable and sat down again in front of his immobile and incredibly sensitive feet and reached into my box to choose a toy…still 45 minutes left to go…
…so there i sat in the grass on that beautiful tuesday afternoon, close enough to those smooth, bound soles of mike’s to smell the sweat produced during our basketball tournament. i was giving him a minute to catch his breath after only ten minutes of tickling. he was wrecked, and his torture had only begun!!! he hadn’t said a word since i showed him my box of goodies. i just sat and watched his chest rise and fall as he tried to catch his breath. he was breathing loudly, gulping in air. man, this guy was ticklish!! i think being tied up and completely helpless had made him even more susceptible to this form of punishment.
suddenly i heard him ask “so’s that it? am i done?”.
that tinge of desperate hope in his voice made my cock a little harder still, and i couldn’t help dashing his hopes against the rocks! ,”oh no, mike…i’m not even close to being done with you yet! it’s only been ten minutes so far (the little break i just gave you doesn’t count). you’ve still got fifty minutes left, tuff-guy!”, and with that i pulled 6 toothpicks from the box…
first i took a single toothpick and began to jab the soft flesh of his immovable soles with it’s sharp wooden point. i watched his face while i continued to poke him with it. he bit his lip and squeezed his eyes tight. i could tell he was trying not to react, but the sight of him struggling to maintain his composure was just as erotic to me as his outright tortured laughter had been earlier. if his plan was to make me bored with the session, it was failing miserably. i noticed that when i jabbed the point on the apparently VERY sensitive spot between his big and first toes, that his lips trembled slightly and he’d bite down harder on his lip, scrunching his handsome face even tighter! ah ha, a secret spot! i, of course, immediately began to concentrate on this area of both feet. i even picked up a second toothpick so that i could stimulate both hot spots at the same time. as soon as i had doubled my efforts i saw every muscle in his body become even more rigid, his arms and legs trying in vain to pull themselves free of their inescapable bondage. his breathing got harder and came faster! i could tell he was about to lose it, so i began poking even harder and more rapidly!
his face contorted in agony, sweat pouring down his forehead, he opened his mouth wide:
“OHHHHHHHHhhhhGOD….aaaaaaaaHAHAHAAArrrgh…JEEEeeezusgaaaaaahdaaaahaaa argrrrga,,,HEEEEEEeeeheeeeeehahaarg…pleeeeeze sthaaaaaaaaap…!!!”
“oh god, man”, he managed to say between big gulps of air, “that was fuckin’ horrible! thanx for stopping man, i was about to lose my mind. now please, hurry up and untie me, my toes are really starting to hurt!!”
i shook my head slowly, with what must have been an evil grin spreading across my face, “good try mike, but you know the wager was for an hour.”
“but surely it must be close to an hour, couldn’t you be a sport and knock the last few minutes off. seriously, i think i’ll lose my mind if you do this anymore.”
wow! this REALLY must be hell for him, i’d only been poking his feet with the toothpicks for 5 minutes. apparently the intense torment had distorted his since of time. i let him in on the facts with relish, and told him he still had 45 minutes to go. i also made it clear that i was going for the entire hour no matter what. it looked again like he was about to cry. “NOOOOOOOOOOO, PLEEEEEZE… that can’t be true! i KNOW it’s been longer than that! it HAS to have been!!…”
i showed him the stop watch i’d been keeping time with and i swear i think his eyes watered up a little. i sat back down on the grass in front of those tender, trapped soles. this time i pulled out the battery-powered toothbrush and switched it on. he lifted his exhausted head from the chair to look down and see what the noise was. when he saw me with the toothbrush on, only inches away from his helpless feet he lost it! he jerked and bucked against his restraints which refused give at all. “nonononononooooooo…”
and i hadn’t even made contact with the toothbrush yet!! i had an idea. “i’ll make a deal with ya, though…if you can keep from laughing for another five minutes, i’ll let you have another break”……
the battery-powered toothbrush hummed in the hot summer air and mike stared at me wild-eyed, shaking his head slowly back and forth, trying desperately to get me to change my mind. yeah, right!! there was NO WAY i’d pass on even a second of such a great opportunity! this was the first time i’d actually tickle TORTURED another guy and i was having a blast!!! i lowered the toothbrush to the trapped and stretched flesh on the instep of his left foot…
“NOOOOOO, n-n-n-ooooh, ho, ho, haaarghahahaaaaa, heee, h-h-heeshit! shit! god! pleeeze-hee hee hee, no more hahaaargh!!!…”
the sounds were like music to my ears! without letting up for a second i reminded him, “mike, remember, you don’t get your break till you can keep it in for a solid 5 minutes…heh, heh, heh!”
“no please..b-b-break n-n-n-owww! now please. b-b-break?”
“no way, mike!!! you’ve got to earn it!”
“o-o-oKAY ahhh! i w-w-won’t. la-la-laugh!!!”, he bit his lip again and i heard no sounds except the creaking of the metal chair as he pulled on his restraints, and the sound of air being sucked through his sexy, trembling lips…and, of course, the lovely hum of the toothbrush as i slowly let it travel up from his arch to that valley where his toes met the ball of his foot. the closer i got the louder his breathing got. his big toes were held splayed apart from his other toes due to their individual bondage, so once the toothbrush made it into that valley, i let it travel into that hellishly sensitive spot between his big and first toe. his chest began rising and falling more violently and i didn’t hear any laughing but i did hear something that sounded like wh impering…
i fixed the toothbrush so that it wouldn’t fall from between his toes while it vibrated. wedged it in good. then i moved to the other end of the chair to get a good look at his face while i left the toothbrush humming away…
i sat down beside him in the grass and looked at his handsome face trapped there between his stretched and bound arms. his face was red, sweat was running in rivulets down his cheeks, and tears of frustration and effort had actually welled up in his eyes, mixing with the sweat streaming from his pores. he looked at me intensely and i could see he wanted to say something, but was afraid to open his mouth for laughing. i guessed what it was, looked at my watch and said, “just 2 minutes to your break mike, you can make it.” i brushed some strands of sweaty, matted hair away from his drenched forehead and smiled, “well, i better get back to work”. mike whined loudly in protest as i got up and returned to the toothbrush still buzzing away between his poor toes. i left the toothbrush where it was and picked up one of the melting ice cubes instead. i began to tickle the sole of his right foot with the ice, and he must not have been expecting that extra sensation because he immediately lost what control he’d managed to maintain and busted out laughing: “NOOOHOOOHOHOHEEEEE, oh-oh-oh-GAAAAAHD noooohohohahahaaaarggh, aaaahahahaaaargh…”
“awwwww, mike”, i said in mock-sympathy, without stopping, ” you lost your break. now you’ll have to start all over…”
the ice had gotten such a great reaction that i decided to abandon the toothbrush for now and pick up a second ice cube. while continuing to swirl the first cube around the sole of his helpless foot i added his other foot into the mix as well. two ice cubes now, sliding sadistically up and down those taut arches, eliciting shrieks and unceasing laughter from my handsome victim. his whole body had tensed even more at this new phase of the torture, he bucked as much as he could (almost not at all) in his bondage: “oh god, oh god, ohgodohgodohgod….mmmmrgh, mmmmrgh, ah ah ah ahahahaaaaaa, ha ha haaaarrgh…!” “now, now, mike you want that break, don’t you, tuff-guy?”, i taunted my tortured friend. he shook his head earnestly up and down. “yes, y-y-yessss!!! b-b-b rea-aye-aye-ayeyahahahaaaa…”, he could barely form intelligible words now. “well then i suggest you get hold of yourself, bud, and STOP LAUGHING or you’ll never earn that break. five minutes, remember? no laughing!” “i c-c-can’t. i can’t s-s-s-top!! ah ah ahahaaa aaaaaaah ha ha haaraghaa…” “i suggest you try”, i answered putting all my concentration back to those sexy, vulnerable feet. i gave him just a second to catch his breath and bite down on his bottom lip again before placing each cube against a heel and slowly dragged them up the length of his soles… once again, i heard no laughing, only moaning sounds as his struggled to keep the agonized laughter from escaping his trembling lips and the sound of the iron chair groaning under the stress of a bound and struggling boy! his bound soles were wet now, from the melting ice. the tightly stretched skin gleamed in the sunlight, drops of cold water running in trails down his instep (hopefully adding to the ticklish sensations). they looked gorgeous! i changed positions so that i was lying on my stomach in the grass with my face so close to his trapped soles that i could smell them. this way i could press my hard cock against the ground through my shorts, while i continued to torture mike. it felt so good!! the pressure on my cock, the closeness of his bare, twitching feet! i could have cum in a second, but i held off. i still had a little more than a half hour of this torture left to inflict. i decided that if i was going to cum i’d do it in the last few seconds of his torture (okay, so i’m a little bit of a masochist, as well). since mike was way too preoccupied with desperately trying not to laugh to notice anything but the tormenting sensations of the ice, i took this opportunity to gingerly extend my tongue and move my head in close enough to push it in between the big and first toe of his right foot. this close i could really smell the hot sweat from the basketball game and i tasted the salty flesh of his taut, trembling flesh. i drew back. i had to! i was about to cum but wanted to wait and there was no way i’d have been able to hold back if i’d kept my tongue between those delicious toes. i sat back upright and abandoned his arches for his toes and the hyper-sensitive valley just below them. as soon as i’d guided the slippery ice cubes up to those toes, mike groaned loudly:
“MMMMMRGRRRRRGHHH AAAAAAAAH GOD GOD GOD THAT’S C-C-C-COLD!!! H-H-HOW L-L-L-ONG BEFORE THE BRE-BREAK?” i looked at my watch. ooops! i’d been so entranced with the close-up tickling and stolen licks at his toes that i’d lost track of time. it’d been almost ten minutes since he’d allowed himself to laugh. “sorry, mike, you earned your break a few minutes ago”, i stopped the tickling. “you mean it’s been longer than five minutes!?!” “sorry.” “YOU JACK-ASS!!” he yelled at me. i decided he’d pay for that after his break….
since i’d gone against my word and let mike continue his struggle not to laugh past the stated 5 minutes i decided to give him a 2 minute break instead of only 60 seconds. as i sat in the warm grass, listening to mike trying to catch his ragged breath, and staring at the soles of his feet so helplessly bound my hand trailed across the ground and came across the socks i’d pulled from his feet about a half hour ago. they’d gotten so soaked with sweat during the basketball game that they’d become stiff as they dried in the afternoon air. since mike had his eyes shut, trying to regain his composure and milk every bit of relaxation he could out of his 2 minutes, i took the opportunity to pick up one of his sweatsocks and smell it, breathing deeply the heavy scent of old rubber and leather from his sneaker, and the pungent sweat from his foot. it reeked! much worse than the scent i’d picked up from the surface of his barefoot when i leaned in close. i had an idea. looking at my watch, i piped up “Break’s over, dude!…” i heard mike groan softly in dread. i snatched up both socks and got up to move to the top of the chair where i found mike’s face, still sweating, between his arms. “we’re gonna change the way we’re doing things here, okay?”, i asked my victim/friend. he nodded eagerly “no more tickling?”, he asked hopefully. “actually…”, i responded with my slyest of smiles, “i was thinking ‘no more breaks’ ” his smile immediately dropped off his face to be replaced by a priceless look of sheer horror. i explained that it was just that he was my best friend and i couldn’t stand to prolong his agony any longer. it’d be over much quicker if i just went for the solid last 30 minutes all at once instead of stretching it out with all these interrupting breaks… “NO!!!…PLEASE, NO!!…NONONONO…” i easily shut him up by pulling out a roll of electrical tape and securely taped his mouth shut. then i pulled up his dirty socks so that he could see them. he looked confused. i tied the toes of the long sweatsocks together. he still looked at me in confusion and enforced silence. i then began to bring the now linked dirty socks closer to his face. he suddenly understood and began shaking his head violently from side to side as much as he could, sandwiched between his tied arms. alas, to no avail, i eventually got the socks over his face and tied them in a knot behind his head. i made sure to position the filthy knot made at the toes so that it directly covered his nostrils. to test my plan, i now used both hands to grab into his ribs! since he couldn’t laugh through his taped lips, he was forced to take deep breaths through his nose and smiled when i saw his eyes squeeze tight at being forced to smell the odor of his own pungent feet! my fingertips glided up to his pits, making unendurable ticklish spirals there while i watched him forced to smell his socks…he begged me with his eyes. poor boy…. 😉 pulling out two hairbrushes i went back down to his trapped feet, “ready for your last half hour, tuff-guy?” the only answer i got was a panicked sounding muffled protest, but i couldn’t make it out…best just to ignore it, i decided, and went to work.
the brushes i’d selected had very stiff bristles. hundreds of them!! i placed a brush at each heel and s-l-o-o-o-w-l-y dragged them both up the surfaces of each hopelessly stretched and bound sole. the stiff bristles against the soft, tender flesh of his arches got the reaction i’d been hoping for. every muscle of the poor boy’s body looked like corded rope flexing uselessly beneath his sweating flesh. his body was involuntarily exerting all of it’s might against the bonds and yet did absolutely nothing as far as helping him out of his hellish predicament!! when the brushes had made it to the center of both soles, i began to spiral the cruel bristles in torturous circles over and over. he couldn’t handle it. for the first few seconds, he’d managed to take only very shallow breaths through his nose (since his lips were still taped) in order, i assumed, to keep fromgetting too big a whiff of his own filthy socks still tied tightly over his nose. but when i started in circling his insteps with the fiendish hairbrushes he let out a load moan and i heard him suck air ferociously and involuntarily through the sock-filter. i saw his face scrunch up in disgust as the odor hit him full-force again! he immediately tried taking shallow breaths again, but i was having way too much fun with this and decided to pick up the speed and pressure of the brushes. in a matter of seconds i had him groaning hysterically under his gag and taking in one stinking lung-full of air after another! i was having the time of my life!! i kept that up for about fifteen minutes, listening to the frantic sounds mike made. sounds that would have been nothing but pitiful begging if i had taken off the gag and let him form actual words. then i had yet another sadistic idea and reached into the toys i’d brought from the house and pulled out a pair of long, sharp-tipped scissors. i opened them a little, giving me two tips to work with. i chose his right foot and placed each of the two points in contact with either side of the ball of his foot, just under the toes. i used just enough pressure to cause a thin white line to appear behind each of the scissors’ tips as i slowly dragged them down the surface of his soles. i could tell mike found the sensation unbearable because, even though he couldn’t move his feet at all i could see the muscles in the sole of his right foot twitching and spasming under the tautly stretched flesh. after a few minutes i switched to the other foot and inflicted the same torture there.
looking at my watch, i realized i only had 15 minutes left. i suddenly stopped torturing mike with the scissors and used them to cut the laces binding his toes back to his ankles. i heard a sigh of relief come from under the tape as he immediately began flexing his stiff toes. then i moved up to his head and pulled off the socks and slowly peeled the tape from his sexy lips.
“THANK GOD THAT’S OVER!!!”, he mistakenly assumed, his face stained with tears of agony and pouring sweat, “i don’t think i could’ve taken one more second!!!”
i let a smile slowly creep over my face and shook my head as i looked down at his pitiful sweat-drenched form stretched so tight and vulnerably across the iron chair, ” it’s STILL not quite over mike”, i showed him the watch, “i’ve got ten minutes left. it’s just that i’ve decided to concentrate on our armpits and ribs for the last part and i wanted to be able to hear you laugh and watch your toes flexing while you suffered!” without giving him a chance to respond, i immediately placed myself behind the chair where i had a perfect view of his feet still bound at the ankles to the bottom of the chair and dove into his sweaty pits with all ten fingers at once!!
“Aaaaaarrrgh oh God, oh God, oh oh oh shit!!! ah-ah-ah-ahahahaaaa!!heeeeeeeeehahahaaaargh…! no please, no pluh-pluh-please,ple-hee-hee-hee-eeze!! i c-c-can’t t-t-take anymore ha hahaaaaaargh…PLEASE STAAAAAHP…!”
his reaction was wonderful! that deep, helpless laughter and screaming bubbling from his sexy lips involuntarily. he knew it was what i wanted to hear and yet he still couldn’t keep himself from begging and laughing. my cock had become absolutely rigid and i pressed it against the iron bar at the top of the chair where mike’s wrists were so soundly lashed. i pressed against the bar (where mike couldn’t see me) even harder and continued tickling his pits and ribs with my fingers while focusing my eyes on his toes wiggling in ticklish agony at the other end. in the midst of another gale of mike’s helpless laughter i came hard against the chair, his hysterical laughter blocking out the long moan of sheer pleasure that i couldn’t help producing as i finally brought myself off.
after i’d got my composure back, i let mike know it was over and untied him. he immediately jumped up off the chair and stretched his aching limbs, sweat beading down his almost naked body, and promised that he would get his revenge one day…one day soon!
my blood ran cold at the thought! i was so into torturing him that it never occurred to me that he might eventually have me at his mercy!! oh jeeeeze…
well that’s it for mike’s ordeal and the consequences of our first tickling-wager.